Subko, KarolinaKildgaard, SaraVicente, FranciscaReyes, FernandoGenilloud, OlgaLarsen, Thomas O2025-01-072025-01-072021-01-20https://hdl.handle.net/10668/24600The marine-derived fungus Stilbella fimetaria is a chemically talented fungus producing several classes of bioactive metabolites, including meroterpenoids of the ascochlorin family. The targeted dereplication of fungal extracts by UHPLC-DAD-QTOF-MS revealed the presence of several new along with multiple known ascochlorin analogues (19-22). Their structures and relative configuration were characterized by 1D and 2D NMR. Further targeted dereplication based on a novel 1,4-benzoquinone sesquiterpene derivative, fimetarin A (22), resulted in the identification of three additional fimetarin analogues, fimetarins B-D (23-25), with their tentative structures proposed from detailed MS/HRMS analysis. In total, four new and eight known ascochlorin/fimetarin analogues were tested for their antimicrobial activity, identifying the analogues with a 5-chloroorcylaldehyde moiety to be more active than the benzoquinone analogue. Additionally, the presence of two conjugated double bonds at C-2'/C-3' and C-4'/C-5' were found to be essential for the observed antifungal activity, whereas the single, untailored bonds at C-4'/C-5' and C-8'/C-9' were suggested to be necessary for the observed antibacterial activity.enAttribution 4.0 Internationalhttp://creativecommons.org/licenses/by/4.0/MS/HRMSascochlorinbioactivitydereplicationmeroterpenoidsAlkenesAnti-Bacterial AgentsAntifungal AgentsCandida albicansHypocrealesPhenolsStaphylococcus aureusresearch article33498522open access10.3390/md190200461660-3397PMC7909580https://www.mdpi.com/1660-3397/19/2/46/pdf?version=1611635583https://pmc.ncbi.nlm.nih.gov/articles/PMC7909580/pdf